WOLFVILLE’S DEEP ROOTS MUSIC Festival has brought its share of stellar talent to the Annapolis Valley in its near-decade of existence, but it tops itself in the songwriter sweepstakes this weekend with a visit by the one and only Loudon Wainwright III.

Of course, the sardonic folk icon’s Saturday night show at Acadia University’s Convocation Hall isn’t the only reason to spend some time in this cosy college town between now and Sunday; there’s a fine roster of talent from the Maritimes and across the country.

But Wainwright is a force to be reckoned with, still at the top of his game after 42 years, 22 studio albums, three concert recordings, a few compilations and the obligatory box set.

While certain songs demand to be played — it’s hard to imagine an encore that doesn’t include Dead Skunk — it does make you wonder how you put a show together with so much music to choose from.

“There are a lot of songs,” agrees Wainwright, who, aside from a hiatus after the death of his mother in 1997, has never really stopped writing.

“Some of them I’ve forgotten, or grown tired of doing, and these days I’m singing quite a bit from the new album, Older Than My Old Man Now. But I also have some newer songs that I’ll be playing, and I do dip back into the catalogue.

“A couple of nights ago, I did a show in Pittsburgh so I went back to my very first album and relearned a song called Ode to a Pittsburgh, just so I could sing it there. So occasionally I will familiarize myself with forgotten material, for whatever reason.”

A comparison is made to John Prine, a performer of similar vintage and skill, whose audience will shout out favourite song titles even if they know full well that he’s not leaving the stage without singing Angel From Montgomery or Hello In There.

Wainwright feels he plays for a slightly different crowd, one that knows he has to make the shows interesting for himself in order to take them on a meaningful journey. After all, he is one of the most autobiographical songwriters around, and each record marks a new chapter full of fresh observations.

“I’ve chronicled my particular life since I first started writing songs, and I certainly don’t hide that fact,” he says. “I happen to be very interested in my own life, obsessed even, but the trick is that what’s happening to me is happening to you, and there’s a strong identification factor.

“In that way, my life is fairly generic; it’s not different from a lot of other lives. I just encapsulate it and present it in a three-minute song and hope that the listener will be engaged and feel something.”

Now 66, Wainwright penned the songs on Older Than My Old Man Now after passing the 64-year mark at which his father, Life magazine editor Loudon Wainwright II, died.

He addressed that passing on his 1992 album History, as he would later take stock of his mother’s death on 2001’s Last Man on Earth, but on Older Than My Old Man Now, he looks at how we measure ourselves against our parents’ legacies, even after they’re long gone.

“In my case, I have the same name as my father had, we went to the same boys boarding school and we both did miserably there,” says Wainwright, referring to St. Andrews in Middleton, Del., most famous as the location for the film Dead Poets Society.

“My father died in 1988, but he’s very heavily featured on this record and in my show, as I do these recitations of these columns that he wrote.

“I also do something that’s not on the record, and that’s an entire column that he wrote in 1972, which takes about 10 minutes to recite. He’s kind of a guest star at my show now, and the audience seems very interested in that aspect of my life, and it’s a thrill to be able to sort of collaborate with him.”

Besides collaborating with his father, there are also contributions from his musical offspring, Rufus and Martha Wainwright and Lucy Wainwright Roche, mentor Ramblin’ Jack Elliott, jazz guitarist John Scofield and the esteemed personage of Dame Edna Everage on one eyebrow-raising number, I Remember Sex.

There are songs about family intertwined with wry views on health and mortality, but Wainwright says none of these themes will be new to anyone familiar with his broad discography.

“The first line of the first lyric on my debut album is ‘In Delaware when I was younger,’ so I’ve been somewhat age-obsessed for a while,” he says.

“On the new record, there’s a song that I wrote with Kate McGarrigle, Over the Hill, and we were all of 28 years old when we wrote that. So thinking about getting older, being older and the end of things has always been there.

“But on this record, I decided to make a full-frontal assault on the subject, and the trick, or the predicament, was to somehow make it not a bummer, so we have the novelty songs and guest singers, which I think lightens the load. ‘Death and decay, man, here it is.’”

Until the inevitable occurs, Wainwright continues to enjoy writing, recording and touring, plus the occasional acting gig (most recently he appeared as Uncle Max in the Atlantic Film Festival offering Sleepwalk With Me, from comedian Mike Birbiglia).

As long as the songs remain insightful, tuneful and funny, retirement isn’t an option he’s ready to consider.

“I like my job, you know? Performing is what I always wanted to do, and I like showing off, so that worked out for me, being able to do this for other people and get paid for it.

“In the 75 to 90 minutes that I’m on stage, or over 50 minutes of an album, I try to make it as energetic and interesting as I can. I’m not like that all the time, but that’s what I’m going for, and hopefully it works.”